Synthesis of 1-(2'-O-Methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical Applications

Synthesis of the title compound,1-(2'-O-methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo-[4,5-d]pyridazine-4,7(5H,6H)-dione (1), is reported. It was synthesized in four steps, starting from methyl 1-(ÃƒÂŸ-D-ribofuranosyl)imidazo-4,5-dicarboxylate (2). The 3',5'-hydroxyl groups of 2 was protect...
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Gespeichert in:

Autor*in:	Ramachandra S. Hosmane [verfasserIn] Huan-Ming Chen [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2001

Schlagwörter:	Synthesis Nucleoside Analogue Imidazo[4 5-d]pyridazine 2'-O-Methyl Nucleoside Introduction

Übergeordnetes Werk:	In: Molecules - MDPI AG, 2003, 6(2001), 3, Seite 203-207
Übergeordnetes Werk:	volume:6 ; year:2001 ; number:3 ; pages:203-207

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/60300203

Katalog-ID:	DOAJ06660365X

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author_variant	r s h rsh h m c hmc
matchkey_str	article:14203049:2001----::yteio1oehlrbfrnslhmdz4dyiaie7hhinaatatvbidnbokoat
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allfields	10.3390/60300203 doi (DE-627)DOAJ06660365X (DE-599)DOAJ9551513152574a7f8177a6b107708bdb DE-627 ger DE-627 rakwb eng QD241-441 Ramachandra S. Hosmane verfasserin aut Synthesis of 1-(2'-O-Methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical Applications 2001 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Synthesis of the title compound,1-(2'-O-methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo-[4,5-d]pyridazine-4,7(5H,6H)-dione (1), is reported. It was synthesized in four steps, starting from methyl 1-(ÃƒÂŸ-D-ribofuranosyl)imidazo-4,5-dicarboxylate (2). The 3',5'-hydroxyl groups of 2 was protected with a bis-silylating agent to form 3, which was then methylated to form the corresponding 2'-O-methyl derivative 5. The silyl deprotection of the latter (to form 6), followed by treatment with hydrazine afforded the target nucleoside 1. The reported nucleoside has potentially beneficial applications in biomedicine based on antisense and triple-helical nucleic acid technologies. Synthesis Nucleoside Analogue Imidazo[4 5-d]pyridazine 2'-O-Methyl Nucleoside Introduction Organic chemistry Huan-Ming Chen verfasserin aut In Molecules MDPI AG, 2003 6(2001), 3, Seite 203-207 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:6 year:2001 number:3 pages:203-207 https://doi.org/10.3390/60300203 kostenfrei https://doaj.org/article/9551513152574a7f8177a6b107708bdb kostenfrei http://www.mdpi.com/1420-3049/6/3/203/ kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 6 2001 3 203-207
spelling	10.3390/60300203 doi (DE-627)DOAJ06660365X (DE-599)DOAJ9551513152574a7f8177a6b107708bdb DE-627 ger DE-627 rakwb eng QD241-441 Ramachandra S. Hosmane verfasserin aut Synthesis of 1-(2'-O-Methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical Applications 2001 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Synthesis of the title compound,1-(2'-O-methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo-[4,5-d]pyridazine-4,7(5H,6H)-dione (1), is reported. It was synthesized in four steps, starting from methyl 1-(ÃƒÂŸ-D-ribofuranosyl)imidazo-4,5-dicarboxylate (2). The 3',5'-hydroxyl groups of 2 was protected with a bis-silylating agent to form 3, which was then methylated to form the corresponding 2'-O-methyl derivative 5. The silyl deprotection of the latter (to form 6), followed by treatment with hydrazine afforded the target nucleoside 1. The reported nucleoside has potentially beneficial applications in biomedicine based on antisense and triple-helical nucleic acid technologies. Synthesis Nucleoside Analogue Imidazo[4 5-d]pyridazine 2'-O-Methyl Nucleoside Introduction Organic chemistry Huan-Ming Chen verfasserin aut In Molecules MDPI AG, 2003 6(2001), 3, Seite 203-207 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:6 year:2001 number:3 pages:203-207 https://doi.org/10.3390/60300203 kostenfrei https://doaj.org/article/9551513152574a7f8177a6b107708bdb kostenfrei http://www.mdpi.com/1420-3049/6/3/203/ kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 6 2001 3 203-207
allfields_unstemmed	10.3390/60300203 doi (DE-627)DOAJ06660365X (DE-599)DOAJ9551513152574a7f8177a6b107708bdb DE-627 ger DE-627 rakwb eng QD241-441 Ramachandra S. Hosmane verfasserin aut Synthesis of 1-(2'-O-Methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical Applications 2001 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Synthesis of the title compound,1-(2'-O-methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo-[4,5-d]pyridazine-4,7(5H,6H)-dione (1), is reported. It was synthesized in four steps, starting from methyl 1-(ÃƒÂŸ-D-ribofuranosyl)imidazo-4,5-dicarboxylate (2). The 3',5'-hydroxyl groups of 2 was protected with a bis-silylating agent to form 3, which was then methylated to form the corresponding 2'-O-methyl derivative 5. The silyl deprotection of the latter (to form 6), followed by treatment with hydrazine afforded the target nucleoside 1. The reported nucleoside has potentially beneficial applications in biomedicine based on antisense and triple-helical nucleic acid technologies. Synthesis Nucleoside Analogue Imidazo[4 5-d]pyridazine 2'-O-Methyl Nucleoside Introduction Organic chemistry Huan-Ming Chen verfasserin aut In Molecules MDPI AG, 2003 6(2001), 3, Seite 203-207 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:6 year:2001 number:3 pages:203-207 https://doi.org/10.3390/60300203 kostenfrei https://doaj.org/article/9551513152574a7f8177a6b107708bdb kostenfrei http://www.mdpi.com/1420-3049/6/3/203/ kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 6 2001 3 203-207
allfieldsGer	10.3390/60300203 doi (DE-627)DOAJ06660365X (DE-599)DOAJ9551513152574a7f8177a6b107708bdb DE-627 ger DE-627 rakwb eng QD241-441 Ramachandra S. Hosmane verfasserin aut Synthesis of 1-(2'-O-Methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical Applications 2001 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Synthesis of the title compound,1-(2'-O-methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo-[4,5-d]pyridazine-4,7(5H,6H)-dione (1), is reported. It was synthesized in four steps, starting from methyl 1-(ÃƒÂŸ-D-ribofuranosyl)imidazo-4,5-dicarboxylate (2). The 3',5'-hydroxyl groups of 2 was protected with a bis-silylating agent to form 3, which was then methylated to form the corresponding 2'-O-methyl derivative 5. The silyl deprotection of the latter (to form 6), followed by treatment with hydrazine afforded the target nucleoside 1. The reported nucleoside has potentially beneficial applications in biomedicine based on antisense and triple-helical nucleic acid technologies. Synthesis Nucleoside Analogue Imidazo[4 5-d]pyridazine 2'-O-Methyl Nucleoside Introduction Organic chemistry Huan-Ming Chen verfasserin aut In Molecules MDPI AG, 2003 6(2001), 3, Seite 203-207 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:6 year:2001 number:3 pages:203-207 https://doi.org/10.3390/60300203 kostenfrei https://doaj.org/article/9551513152574a7f8177a6b107708bdb kostenfrei http://www.mdpi.com/1420-3049/6/3/203/ kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 6 2001 3 203-207
allfieldsSound	10.3390/60300203 doi (DE-627)DOAJ06660365X (DE-599)DOAJ9551513152574a7f8177a6b107708bdb DE-627 ger DE-627 rakwb eng QD241-441 Ramachandra S. Hosmane verfasserin aut Synthesis of 1-(2'-O-Methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical Applications 2001 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Synthesis of the title compound,1-(2'-O-methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo-[4,5-d]pyridazine-4,7(5H,6H)-dione (1), is reported. It was synthesized in four steps, starting from methyl 1-(ÃƒÂŸ-D-ribofuranosyl)imidazo-4,5-dicarboxylate (2). The 3',5'-hydroxyl groups of 2 was protected with a bis-silylating agent to form 3, which was then methylated to form the corresponding 2'-O-methyl derivative 5. The silyl deprotection of the latter (to form 6), followed by treatment with hydrazine afforded the target nucleoside 1. The reported nucleoside has potentially beneficial applications in biomedicine based on antisense and triple-helical nucleic acid technologies. Synthesis Nucleoside Analogue Imidazo[4 5-d]pyridazine 2'-O-Methyl Nucleoside Introduction Organic chemistry Huan-Ming Chen verfasserin aut In Molecules MDPI AG, 2003 6(2001), 3, Seite 203-207 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:6 year:2001 number:3 pages:203-207 https://doi.org/10.3390/60300203 kostenfrei https://doaj.org/article/9551513152574a7f8177a6b107708bdb kostenfrei http://www.mdpi.com/1420-3049/6/3/203/ kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 6 2001 3 203-207
language	English
source	In Molecules 6(2001), 3, Seite 203-207 volume:6 year:2001 number:3 pages:203-207
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topic_facet	Synthesis Nucleoside Analogue Imidazo[4 5-d]pyridazine 2'-O-Methyl Nucleoside Introduction Organic chemistry
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container_title	Molecules
authorswithroles_txt_mv	Ramachandra S. Hosmane @@aut@@ Huan-Ming Chen @@aut@@
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callnumber-first	Q - Science
author	Ramachandra S. Hosmane
spellingShingle	Ramachandra S. Hosmane misc QD241-441 misc Synthesis misc Nucleoside Analogue misc Imidazo[4 misc 5-d]pyridazine misc 2'-O-Methyl Nucleoside Introduction misc Organic chemistry Synthesis of 1-(2'-O-Methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical Applications
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topic_title	QD241-441 Synthesis of 1-(2'-O-Methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical Applications Synthesis Nucleoside Analogue Imidazo[4 5-d]pyridazine 2'-O-Methyl Nucleoside Introduction
topic	misc QD241-441 misc Synthesis misc Nucleoside Analogue misc Imidazo[4 misc 5-d]pyridazine misc 2'-O-Methyl Nucleoside Introduction misc Organic chemistry
topic_unstemmed	misc QD241-441 misc Synthesis misc Nucleoside Analogue misc Imidazo[4 misc 5-d]pyridazine misc 2'-O-Methyl Nucleoside Introduction misc Organic chemistry
topic_browse	misc QD241-441 misc Synthesis misc Nucleoside Analogue misc Imidazo[4 misc 5-d]pyridazine misc 2'-O-Methyl Nucleoside Introduction misc Organic chemistry
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title	Synthesis of 1-(2'-O-Methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical Applications
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title_full	Synthesis of 1-(2'-O-Methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical Applications
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author_browse	Ramachandra S. Hosmane Huan-Ming Chen
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title_sort	synthesis of 1-(2'-o-methyl-ãƒâÿ-d-ribofuranosyl)-1h-imidazo[4,5-d]pyridazine-4,7(5h,6h)-dione: an attractive building block for antisense and triple-helical applications
callnumber	QD241-441
title_auth	Synthesis of 1-(2'-O-Methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical Applications
abstract	Synthesis of the title compound,1-(2'-O-methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo-[4,5-d]pyridazine-4,7(5H,6H)-dione (1), is reported. It was synthesized in four steps, starting from methyl 1-(ÃƒÂŸ-D-ribofuranosyl)imidazo-4,5-dicarboxylate (2). The 3',5'-hydroxyl groups of 2 was protected with a bis-silylating agent to form 3, which was then methylated to form the corresponding 2'-O-methyl derivative 5. The silyl deprotection of the latter (to form 6), followed by treatment with hydrazine afforded the target nucleoside 1. The reported nucleoside has potentially beneficial applications in biomedicine based on antisense and triple-helical nucleic acid technologies.
abstractGer	Synthesis of the title compound,1-(2'-O-methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo-[4,5-d]pyridazine-4,7(5H,6H)-dione (1), is reported. It was synthesized in four steps, starting from methyl 1-(ÃƒÂŸ-D-ribofuranosyl)imidazo-4,5-dicarboxylate (2). The 3',5'-hydroxyl groups of 2 was protected with a bis-silylating agent to form 3, which was then methylated to form the corresponding 2'-O-methyl derivative 5. The silyl deprotection of the latter (to form 6), followed by treatment with hydrazine afforded the target nucleoside 1. The reported nucleoside has potentially beneficial applications in biomedicine based on antisense and triple-helical nucleic acid technologies.
abstract_unstemmed	Synthesis of the title compound,1-(2'-O-methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo-[4,5-d]pyridazine-4,7(5H,6H)-dione (1), is reported. It was synthesized in four steps, starting from methyl 1-(ÃƒÂŸ-D-ribofuranosyl)imidazo-4,5-dicarboxylate (2). The 3',5'-hydroxyl groups of 2 was protected with a bis-silylating agent to form 3, which was then methylated to form the corresponding 2'-O-methyl derivative 5. The silyl deprotection of the latter (to form 6), followed by treatment with hydrazine afforded the target nucleoside 1. The reported nucleoside has potentially beneficial applications in biomedicine based on antisense and triple-helical nucleic acid technologies.
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title_short	Synthesis of 1-(2'-O-Methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical Applications
url	https://doi.org/10.3390/60300203 https://doaj.org/article/9551513152574a7f8177a6b107708bdb http://www.mdpi.com/1420-3049/6/3/203/ https://doaj.org/toc/1420-3049
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up_date	2024-07-03T20:59:29.997Z
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Synthesis of 1-(2'-O-Methyl-ÃƒÂŸ-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazine-4,7(5H,6H)-dione: An Attractive Building Block for Antisense and Triple-helical Applications

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